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UNIVERSITI KUALA LUMPUR

Malaysian Institute of Chemical & Bioengineering Technology


Section of Chemical Engineering Technology

Laboratory Guide

ANALYTICAL &
ORGANIC
CHEMISTRY

This module
provides guidelines for
CLB
10803
safety, Laboratory Report and note

book. Its also providing students with


Laboratory manual for subject of
Analytical & Organic Chemistry (CLB
10803).

FIRST EDITION 2010


Review 2012

Laboratory Information
Before each lab session, you should prepare by reading the lab manual, reference
book and summarized it in a jotter book. We expect you to have a good
understanding of the purpose, details of the procedure, the use of all chemicals
and any significant hazards, and the underlying science of the experiment when
you come to lab.

CONTENTS

Preface

Laboratory Safety Guidelines

Safety Declaration Form

Chemistry Lab Report Format

10

Experiment
1

Saponification Reaction of Fat: Soap Production

13

Analysis of Food Colour

16

Determination of Caffeine in Soft drink

20

Organic Synthesis: Formation of Ester

23

REFERENCES

26

APPENDICES

27

PREFACE
This manual provides laboratory guidelines, safety declaration form, Chemistry Lab Report
guidelines and Laboratory manual for subject of Analytical & Organic Chemistry (CLB
10803).
The primary purpose of this manual is to compile all necessary information regarding
laboratory component in one manual.
Students are compulsory to read and understand all the laboratory guidelines provided in this
manual. The safety declaration form should be submitted to the lecturer/instructor before you
start the first experiment.
In the laboratory report format, there are report writing guidelines and requirements that you
have to follow to produce a good quality of lab report.
Laboratory Jotter Notes you are required to prepare a jotter note for each experiment. In the
jotter note, you have to write the basic information of the experiment, the procedure and all
primary data and observations during the experiment. You should prepare the jotter note
BEFORE coming to the lab and submit to the lecturer/instructor BEFORE you leave the lab
on the day of experiment.

LABORATORY SAFETY GUIDELINES


General Guidelines
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.

Conduct yourself in a responsible manner at all times in the laboratory.


Be familiar with your lab assignment before you come to the lab. Follow all written and
verbal instructions carefully. If you do not understand a direction or part of a procedure,
ask the instructor before proceeding.
No student may work in laboratory alone. The lab instructor or co-coordinator grant
exceptions on a case by case basis.
When first entering a laboratory, do not touch any equipment, chemicals or other
materials in the laboratory area until you are instructed to do so.
Do not eat, drink beverages or chew gum in the laboratory. Do not use laboratory
glassware as containers for food or beverages.
Smoking is not allowed in any indoor area.
No music allowed in the laboratory. Radio (including walkman) and other entertainment
devices are not permitted.
No cellular phone is allowed in this laboratory.
Perform only those experiments authorized by the instructor. Never do anything in the
laboratory that is not called for the laboratory procedures or by your instructor. Carefully
follow all instructions, both written and oral. Unauthorized experiments are prohibited.
Observe good housekeeping practices. Work areas should be kept clean and tidy at all
times.
Horseplay, practical jokes, and pranks are dangerous and prohibited.
Always work in a well-ventilated area.
Bring only your laboratory instructions, worksheets and report to the work area. Other
materials (books, purses, backpacks, etc) should be stored in the cabinet.
Know the locations and operation procedures of all safety equipment including the first
aid kit, eyewash station, safety shower, spill kit and fire extinguisher.
Be alert and proceed with caution at all times in the laboratory. Notify the instructor
immediately of any unsafe condition you observe.
Label and equipment instructions must be read carefully before use. Set up and use the
prescribed apparatus as directed in the laboratory instructions provided by your instructor.
Experiments must be personally monitored at all times. You will be assigned a laboratory
station at which to work. Do not wander around the room, distract other students or
interfere with laboratory experiments or others.
Write your name and equipment use every time you come in to the laboratory in the log
book.
Defeating safety devices or using equipment in a manner other than that which is intended
will be grounds for dismissal from the lab.

Clothing
1.
2.

Safety goggles and safety jacket must be worn whenever you work in lab.
Gloves should be worn whenever you use chemicals that cause skin irritations or need to
handle hot equipment.
3. Mask should be worn every time you prepare the chemicals.
4. Safety shoes and hard hat should be worn at all times while in the laboratory.
5. Contact lenses should not be worn in the laboratory unless you have permission from your
instructor.
6. Dress properly during a laboratory activity.
7. Long hair, dangling jewelry and loose or baggy clothing are a hazard in the laboratory.
Long hair must be tied back and dangling jewelry and loose or baggy clothing must be
secured.
8. Sandal, open-toed shoes, high heels or shoes with holes in the sols will not be worn in the
lab.
9. Short and skirts are not permitted.
10. Instructor and laboratory assistant have a right dismiss to you from the laboratory if they
found that you are not wearing proper safety clothing.

Handling Chemicals
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.

Treat chemicals with respect and understand the chemicals you are using with Material
Safety Data Sheet (MSDS). The MSDS are available in the analytical room.
All chemicals in the laboratory are to be considered dangerous. Do not touch, taste or
smell any chemical unless specifically instructed to do so.
Check the label on chemical bottles before removing any of the contents. Take only much
chemical are you need. Smaller amounts often work better than larger amounts.
Label all containers and massing papers holding dry chemicals.
Never return unused chemicals to their original containers.
Never use mouth suction to fill a pipette. Use pipette bulb or pipette filler.
Acids must be handled with extreme care. Always add acids slowly to water, with slow
stirring and swirling, being careful of the heat produced, particularly with sulfuric acid.
Handle flammable hazardous liquid over a pan to contain spills. Never dispense
flammable liquids anywhere near a flame or source of heat.
Never take chemicals or other materials from the laboratory area.
Take good care when transferring acids and other chemicals from one part of the
laboratory to another. Hold them securely and in the method demonstrated by the
instructor as you walk.
All wastes generated during the course of an experiment must be disposed of according to
the lab instructors directions.
Never mix chemicals in sink drains.
Sinks are to be used only for water and those solutions designated by the instructor.

14. Solid chemicals, metals, matches, filter paper, and all other insoluble materials are to be
disposed of in the proper waste containers, not in the sink.
15. Checks the label of all waste containers twice before adding your chemicals waste to the
container.
16. Cracked or broken glass should be placed in the special container for broken glass.
17. Keep hands away from your face, eyes, mouth and body while using chemicals. Wash
your hands with soap and water after performing all experiments.
Personal Hygiene
1.
2.

Wash hands before leaving the lab and before eating.


Gloves should be removed before leaving the lab, using telephones, or entering common
areas.
Accidents and Injuries

1.
2.
3.
4.

Report any accidents (spill, breakage, etc) or injury (cut, burn, etc) to the instructor
immediately, no matter how trivial it may appear.
If you or your lab partners are hurt, immediately tell to the instructor.
If a chemical should splash in your eye(s), immediately flush with running water from the
eyewash station for at least 20 minutes. Notify the instructor immediately.
Spills should be cleaned up immediately.

Handling Glassware and Equipment


1.

Inserting and removing glass tubing from rubber stopper can be dangerous. Always
lubricate glassware (tubing, thistle tubes, thermometer, etc) before attempting to insert it
in a stopper. Always protect your hands with tower or cotton gloves when inserting glass
tubing into, or removing it from a rubber stopper.
2. When removing an electrical plug from its socket, grasp the plug, not the electrical cord.
3. Hands must be completely dry before touching an electrical switch, plug or outlet.
4. Examine glassware before each use. Never use chipped or cracked glassware.
5. Never use dirty glassware.
6. Do not immerse hot glassware in cold water; it may shatter.
7. Report damaged electrical equipment immediately. Look for things such as frayed cords,
exposed wires and loose connections. Do not use damaged electrical equipment.
8. If you do not understand how to use a piece of equipment, ask the instructor for help.
9. Be careful when lifting heavy objects. Lift comfortably, avoid unnecessary bending,
twisting, reaching out, and excessive weights, lift gradually and keep in good physical
shape.
10. Do not transfer a glassware form one laboratory to another without permission from
instructor.

Heating Substances
1.
2.
3.
4.
5.

Do not operate a hot plate by yourself. Take care that hair, clothing, and hands are a safe
distance from the hot plate at all times. Use of hot plate is only allowed in the presence of
the teacher.
Heated glassware remains very hot for a long time. They should be set aside in a
designated place to cool, and picked up with caution. Use tongs or heat protective gloves
if necessary.
Never look into a container that is being heated.
Do not place hot apparatus directly on the laboratory desk. Always use an insulated pad.
Allow plenty of time for hot apparatus to cool before touching it.
If leaving a lab unattended, turn off all ignition sources and lock the doors.

Ended the Experiments


1.

2.

At the end of the laboratory sessions, you should;


1. Shut-off main gas outlet
2. Turn-off the water inlet
3. Desk top, floor area and sink are clean
4. All equipment is cool, clean and arranged
All equipment use should be flushed using deionized water.

SAFETY DECLARATION FORM


The Dean/Head of Campus
Universiti Kuala Lumpur
Malaysian Institute of Chemical and Bioengineering Technology
Lot 1988, Vendor City Industrial Area
Taboh Naning, 78000 Alor Gajah
Malacca
Dear Sir,
SAFETY DECLARATION
I ... ID
No . declare that I have read and understood the safety rules and
regulations in UniKL MICET. I hereby agree to abide by all the rules and regulations stated in
the safety guidelines.
I hereby understood the contents and will disciplinary action will be taken against me, if I do
not abide by the stated rules.
I am fully responsible for all my actions during laboratory sessions.

Thank you.
Yours faithfully,

.
Name:
Matrix No:
Subject:
Date:
9

CHEMISTRY LAB REPORT FORMAT


Your lab report should be in hand written. Make sure that you check your document for any
spelling errors. Each lab report is worth 100 points. You should also read the student handbook
on the subject of plagiarism. Your data and observations will be similar, but your interpretations
should not be written identically. You may not copy another students lab report in part or in its
entirety. If you are found guilty of this infraction, you and the person from whom you copied will
both lose points or shared total marks. In extreme cases or repeated offenses, both students may
receive a zero for the lab.
Title
Use a separate title page. Include the title of the experiment, YOUR NAME, and the date. Also
clearly indicate the name(s) of your lab partner(s).
Summary/Abstract (not more than 1 page)
It should be written after conclusion of experiment OR project. Its cover briefly about the
Introduction, Objectives, Methodology, Result & discussion and Conclusion.
Objectives
State the objectives of the experiment or report (point form)
Example:
The objective of the experiments was .
Introduction
Background to the work / experiment
Example:
The purpose of this experiment was to identify the present of heavy metal in river water by using
Atomic Absorption Spectroscopy (AAS). AAS is .
Theory / formula used in the experiment. Do not just copy word for word from the lab handout.
The introduction should be of 1 3 pages.
Materials
List the chemicals and equipment needed to perform the experiment.

10

Procedure
Write the procedure in chronological order. Again, DO NOT COPY DIRECTLY from the lab
handout. Rearrange your procedure become a passive sentence.
Example:
Prepare 0.5M NaOH solution (from manual)
0.5M NaOH was prepared (your report)
Result & Discussion
Analyze all data qualitative and quantitative. Then transfer finding into Table, Graph, Histogram
and Pie chart if necessary. This includes any observations. Make sure that your graphs have
titles, labeled axes with units, and legends. You should include the proper units with any
numbers, as well as use the proper number of significant figures based upon the lab equipment
used. DO NOT place any calculations or data analysis in this section. It may be a good idea to
reproduce here any data tables that you completed during the lab. Base on above point, discuss
on your findings and relate to your theory and objective of experiment.
Example:
Table 1: X vs. Y
Samples
A
B
C
D

X (unit)

Y (unit)

Figure 1: Relationship between X and Y


11

Conclusions
This is the most important section. Please include the summary of the results and relate in brief
the findings / results with the theory. Answer the questions, What did you learn?, Did I
accomplish the purpose?, How would I improve the experiment next time?. Recommendation
is optional. The conclusion should be one paragraph of 5 7 sentences.
References
Write down any sources such as
encyclopedia, books, etc. that you used.

your

textbook,

the

Internet,

electronic

A list of lab manuals, books, reports, journal, world wide web (www) etc.
Arrangement (year, alphabetical order)
Author, title, publisher, year, chapter or page number

Example:
Smith J.M and Van Hess H.C., Introduction to Chemical Engineering Thermodynamics,
McGraw-Hill, New York, 2001, p229.
Appendix
Here is where you attach any material that you think is pertinent to the lab report such as
summary of calculation involved. Also answer any questions here that are in the lab report. You
do not have to re-write the questions, but label and number them appropriately.

12

EXPERIMENT 1
SAPONIFICATION REACTION OF FAT: SOAP PRODUCTION

OBJECTIVE

To synthesize a sample of hard soap


To test the soap produced

INTRODUCTION
The procedure of making soap involves the basic hydrolysis (saponification) of a fat.
Chemically, fats are referred to as triglycerides. They contain ester functional groups.
Saponification involves heating fat with an alkaline solution. The alkaline solution hydrolyzes
the fat to alcohol and the salt of a long chain carboxylic acid (soap).When common salt is added,
the soap precipitates. The soap is washed free of unreacted alkaline solution and molded into
bars.
O
R C

CH2

O
R'

CH

O
R'' C

Fat

CH2

3 NaOH
3R

HO

CH2

HO

CH

HO

CH2

+
O

Na

Sodium salt of an acid (soap)

glycerol

13

MATERIAL AND METHODS


Materials
Chemicals:
NaOH
Solution
95% ethanol
4 % calcium chloride solution
Apparatus:
Conical Flasks
Beaker
Filter funnel

50% water/ethanol mixture NaCI


Trisodium phosphate
Fat

Hirsch / Buchner funnel


Watch glass

Methods:
Preparation of Soap
1.

Prepare a NaOH solution (about 0.25 g sodium hydroxide


dissolved in a mixture of 1.0 ml of distilled water and 1.0 ml of 95%
ethanol).

2.

Place about 0.25 g of fat in a 50 ml conical flask and add the


prepared sodium hydroxide solution to the flask.

3.

Heat the mixture in a in a bath of 100oC.

4.

Cover the flask with some aluminum foil to help reduce


evaporation. Swirl the Erlenmeyer flask every few minutes. Use
tong to do this.

5.

The soap will precipitate from the boiling mixture within 20


minutes.

6.

If you observe that some alcohol and water is evaporating from


the flask, you may add up to 0.4 ml of a 50 % water/alcohol
mixture to replace the solvent.

7.

Heat the mixture for a maximum time of 25 minutes.

8.

Place 4 ml of NaCI solution in a 15 ml beaker and transfer the


saponified mixture from flask to beaker.
14

9.

Stir the mixture while cooling the beaker in an ice-water bath.

10.

Collect the prepared soap on a Hirsch funnel of ice cold distilled


water to remove excess NaOH.

11.

Continue to draw air through the filter for a few minutes to partially
dry the product. Test your soap with the procedure below.

Analysis of Data
1.

Remove about 0.01 g of soap from the filter paper and placed it in a
clean 10 ml graduated cylinder

2.

Add 3 ml of distilled water, close the cylinder with your thumb and
shake the mixture vigorously for about 15 sec. After about 30 sec
standing, Record your observation. Note down the level of the
foam.

3.

Add 5 10 drops of 4% calcium chloride solution to the soap


mixture from a Pasteur pipette. Shake the mixture for 15 sec and
allow it to stand for 30 seconds. Record your observation on the
effect of addition the calcium chloride.

4.

Then add 0.5 g of trisodium phosphate and shake the mixture again
for 15 seconds. After 30 sec. Again observe and record the result.

Pre Laboratory Question


1. Give a definition of saponification.
2. Explain how soap can function as dirt remover.
3. Synthetic detergent functions in the same way as soaps. Give the
advantages of synthetic detergent over soaps.

Post Laboratory Question

15

1.

Reaction of fat with NaOH will produced long chain carboxylic


acid (soap) in form of Bar. What would be happen if sodium
Hydroxide (NaOH) is replaced by Potassium hydroxide (KOH).

EXPERIMENT 2

ANALYSIS OF FOOD COLOUR

OBJECTIVE
(1) To determine max of Colourant (wavelength scan)
(2) To prepare a serial dilution and generate a standard calibration
graph for sample quantitation (photometric scan)

INTRODUCTION
Food coloring (colouring) is any substance that is added to food or drink
to change its color. Synthetic Food Colours, also known as Artificial
Food Colours, are manufactured chemically and are the most commonly
used dyes in the food, pharmaceutical and cosmetic industries. Besides
that, a growing number of natural food dyes are being commercially
produced, partly due to consumer concerns surrounding synthetic dyes.
Some examples include Caramel coloring (E150), made from caramelized
sugar, used in cola products and also in cosmetics. Annatto (E160b), a
reddish-orange dye made from the seed of the Achiote. A green dye made
from chlorella algae (chlorophyll, E140) and etc.
All those colourant can be analyze by using an ultraviolet/visible
spectrophotometer. Figure 1.0 below gives a schematic diagram of a
double beam spectrophotometer. Instruments for measuring the
absorption of U.V. or visible radiation are made up of the following
components; Sources (UV and visible), Wavelength selector

16

(monochromator), Sample containers, Detector, Signal processor and


readout.

Figure 1.0

Schematic diagram of double beam UV Vis


spectrophotometer

When a beam of parallel radiation passes through a layer of solution of


thickness, b (cm) and a concentration, C (moles per liter) of an absorbing
species, absorption of radiation occurs. The transmittance (T) of the
solution is the fraction of incident radiation transmitted by the solution.
Transmittance is often expressed as a percentage. The absorbance (A) of a
solution is defined as the negative log of the transmittance (T) of the
solution. The absorbance is directly proportional to the path length of the
radiation through the solution and the concentration of the absorbing
species.

A=bc
Where;

A = absorbance (no unit)

= molar absorptivity coefficient (M-1 cm-1)

= pathlength (cm)

c = concentration (M or mol/L)

This relationship between absorbance, A and bc is known as Beers


Law. Beers Law is successful in describing the absorption behavior of

17

dilute solutions only. At high concentrations, absorbance of the solution


does not obey Beers Law and is no longer proportional to C.
In this experiment you are going to conduct two main applications which
are wavelength scanning and photometric scanning.

MATERIALS AND METHODS


Materials
Chemicals:
100 ppm colorant stock (100 ml), Unknown (two), Distilled water
Apparatus:
Perkin Elmer UV/Vis Spectrophotometer Lambda EZ210, Sample
cuvettes, path length 1 cm, Volumetric flask 50 ml (five), Pipette 5
ml, 10 ml and 25 ml (one each), Rubber bulb (three), Beaker 100 ml
(one), Graduated cylinder 50 ml (one), Dropper (one), Labeling
sticker & Tissue paper.
Methods:

18

1.

Prepare serial dilutions (5 ppm, 15 ppm, 25 ppm, 35 ppm and


45 ppm) in 50 ml volumetric flask from the 100 ppm
carmoisine stock.

2.

After preparing the serial dilutions, your instructor will brief


on the standard operating procedure of Perkin Elmer UV/Vis
Spectrophotometer Lambda EZ210.

3.

Fill a cuvette with 45 ppm dilution and another cuvette with


blank solution; insert them in the sample compartment. Wipe
clean the sides of the cuvettes and remember not to touch on
the clear surface. Do the wavelengths scan and obtain the
max. Record your data..

4.

For photometric scan, fill the cuvette as step no 3 but use the
serial dilution prepared and scan one by one. Record the
absorbance readings and look at the standard calibration graph
produced.

5.

Also determine the concentrations of Unknown #1 and


Unknown #2.

Analysis of Data
The purpose of wavelength scan is to determine at what wavelength the
carmoisine able to absorb in the range of 200 nm to 700 nm. From
spectrum obtain, please identify max .
The purpose of photometric scan is to determine the concentration (single
component) of an unknown sample, after generating a working 'standard
curve' from a series of known standards (known concentration). Record
the absorbance readings for a series of prepared dilution generate
standards calibration curve and identify concentration of unknowns.
All calculation must show in detail.

19

Pre Laboratory Question


1. State the Beers Lambert law.
2. What is the volume needed to prepare a 50 ppm of carmoisine
from a 100 ppm of carmoisine in 100 ml volumetric flask?
Post Laboratory Question
1. Why we need to wipe the sides of the cuvette clear surface?
2. Describe the function of wavelength scanning and photometric
scanning.

EXPERIMENT 3

DETERMINATION OF CAFFEINE IN SOFT DRINK


OBJECTIVE :
1. To Identify the present of Benzoic acid/ Caffeine in soft drink
sample
20

2. To determine amount of caffeine in soft drink sample.

INTRODUCTION:
High Performance Liquid Chromatography (HPLC) is a chemistry based
tool for quantifying and analyzing mixtures of chemical compounds. It
can be used to separate compounds that are dissolved in solution. HPLC
instruments consist of a reservoir of mobile phase, a pump, an injector, a
separation column, and a detector. Compounds are separated by injecting
a plug of the sample mixture onto the column. The different components
in the mixture pass through the column at different rates due to
differences in their partitioning behavior between the mobile liquid phase
and the stationary phase.

The area of this peak (in relation to the area of other peaks) is
proportional to the concentration of that particular species in the sample.
The identity can also be found by comparing the sample peaks to
standards. Identical substances (peaks) will have identical retention
times.
MATERIALS AND METHODS
Materials:

21

Isocratic HPLC system with UV detector, C18 column, Vacuum, Funnel,


0.45 m filter paper
0.45 m filter syringe,100 L syringe,60 mL syringe,Volumetric flask
Chemicals:
Caffeine 1000 ppm standard (stock solution), Methanol (HPLC grade),
Double distilled water (filtered with 0.45 m filter paper), Soft drink
sample
Methods:
1. Preparation of caffeine standards
Prepare standard caffeine samples of 20 ppm, 40 ppm, 60 ppm, 80
ppm and 100 ppm by diluting portions of the 1000 ppm solution
with distilled water.
2. Preparation of soda samples
Obtain a soft drink sample.
Degas the sample by placing it in a vacuum flask and connecting
the flask to a vacuum pump or water aspirator. Leave it under
vacuum until no more bubbles appear in the soda sample. (If no
vacuum is available, allow the soda to stand open overnight)
Filter the degassed soda through #42 filter paper.
3. After preparing the serial dilution and sample, your instructor will brief
on standard operating procedure of HPLC.
Analysis of data
1.
2.
3.
4.

Use standard caffeine retention time to identify the caffeine peak


and then record their retention time.
By using above information, clarify and justify the present of
caffeine in the soda sample.
Record different concentration of standards peaks area and
construct a standard calibration curve (concentration vs peak
area).
Measure the caffeine peak in the soda sample chromatograph, and
use standard calibration curve (concentration vs peak area) to
determine the concentration of caffeine in the soda sample.

Note: All raw data must be record in table form.

22

Pre Lab Questions:


1. Briefly explain how HPLC is used as a separation technique.
2. What are the purposes of the mobile phase and the stationary phase?
3. What is the purpose of the caffeine standards?
Post Lab Questions:
1. Why does the syringe have to be carefully rinsed before each use?
2. Retention of caffeine in standards. How could you be identify a peak
in the soda was caffeine and not another substance by using retention
time?

23

EXPERIMENT 4
ORGANIC SYNTHESIS: FORMATION OF ESTER

OBJECTIVE

To synthesis ethyl acetate (ethyl ethanoate)

INTRODUCTION
Chemist use organic synthesis to make larger amounts of useful natural
compounds and to invent totally new compounds. Depending on the
choice of R and R, we have a variety of the final ester, RCOOR. Small
chain side groups give very aromatic compound, while long chain side
groups form waxy compounds.

O
R C

OH + R'
Carboxylic
acid

OH

heat

alcohol

R C

OR' + H2O
Ester

water

The reaction of a carboxylic acid with an alcohol to produce an ester plus


water is known as the Fisher esterification reaction. A mineral acid,
usually sulfuric acid is used as a catalyst.

MATERIALS AND METHODS


Chemical:
Ethanol, Glacial acetic acid, Conc. sulfuric acid, 30% Sodium carbonate
solution, Calcium chloride, Granular anhydrous Calcium chloride, antibumping granules.
24

Apparatus:
Round bottom flask, Water condenser, retort stand, separating funnel
Methods
1. Set up a reflux system.
2. Mix 50 ml of 95% ethanol and 50 ml of glacial acetic acid thoroughly
in a 250 ml round bottomed flask. Add slowly with cooling and
shaking 10 ml of concentrated H2SO4. Ensure that the mixture is
homogenous, and then fit the flask with a reflux water condenser
and boil the mixture gently for 10 minutes. Cool the flask and its
content.
3. Rearrange the position of the condenser for distillation set up.
4. Put a few boiling chips in the flask. A filter flask, whose side arm is
joined to a rubber tube leading over the edge of laboratory bench, is
used as a receiver. Ethyl acetate is highly flammable. Therefore any
vapors should be conducted off the table towards the floor. Distilled
off about 2/3 of the mixture.
5. Transfer the distillate to a separating funnel and add about 25 ml of
30 % Na2CO3 solution. Stopper the funnel, invert it and shake it,
opening the stopcock from time to time. Allow the two layers to
separate. Carefully run off and reject the lower layer, ensuring
that the sodium carbonate is removed as completely as possible.
6. Prepare a solution of 25 g of calcium chloride in 25 ml of water.
Add if to crude ethyl acetate in the funnel. Shake vigorously. Allow
the mixture to separate. Run off the lower aqueous as completely as
possible.
7. Run the ethyl acetate into a small conical flask. Add a few lumps of
granular anhydrous calcium chloride. Shake occasionally until the
liquid is clear.
8. Decant the liquid some anti bumping granules. Arrange for
distillation (with a 0 100oC thermometer in the apparatus). Pre

25

weight the receiving flask. The distilling flask should be placed in


cold water bath, which is gradually heated.
9. The ether that is always formed in this reaction will distill off at 35
45oC and may be discarded. Continue to heat and collect the fraction
that boils between 74oC and 79oC.
10. Weight your product and calculate the percentage yield.
11. Run FTIR of your product and characterize it smell.
12. Inject substrate and product into Gas chromatography.

Analysis of data
1.

From mass of acid, determine the percent yield of your final product
(Show all calculation in detail)
2. Interpret the FTIR of this compound. Identify the principles peaks.
3. Interpret Gas chromatography result.

Pre Lab Question


1.

Reaction of acetic acid with ethanol to produce will produce ethyl


ethanoate and water. Based on that the reaction, how many grams of
ethyl ethanoate would be produced if 50 ml of ethanol were react
with 50 ml acetic acid? (given ethanol : 0.8 g/ml and acetic acid : 1.06
g/ml and ethyl acetate: 0.9g/ml). Calculate the percentage yield if 50.0
g of ethyl ethanoate was obtained from the experiment.

Post Lab Question


1. What are percent yields? How this can be improves?
2. Based on result above, does the FTIR show any contaminant from
initial reactants? Explain.

26

REFERENCES
1. Francis A Carey, Organic Chemistry, 7th Edition, McGraw Hill
ISBN : 0073311847 / 9780073311845
2. T.W. Graham Solomon,Organic Chemistry, 8th Edition, Wiley
QD253.2.S65 2004
3. Douglas A. Skoog, Donald M. West and F. James Holler,
Fundamentals of Analytical Chemistry, 8th ed., Saunders College
Publishing, 1997.
QD75.22.F86 2003
4. Mohan, Jag, Organic Analytical Chemistry: Theory and Practice,
Alpha Science International, Ltd, 2004
ISBN : 0849339529 / 9780849339523
5. Mohan, Jag, Organic Spectroscopy: Principles and Applications,
Alpha Science International, Ltd.
ISBN : 0849339529 / 9780849339523

27

APPENDICES

28

Mass
1 lbm = 0.453592 kg
1 ton = 2000 lbm
1 kg = 2.20462 lbm
Volume
1 ft3 = 0.028317 m3
1 L = 0.001 m3
1 m3 = 35.32 ft3
1 cm3 = 0.06102 in3
1 gal =0.0037854 m3
1 gal/min = 6.31 x 105 m3/s

Force
1 lbf = 4.448222 N
1N = 0.224809 lbf = 1 kg.m/s2

Density
1kg /m3 = 0.062428 lbm/ ft3

Pressure
1 pascal (Pa) = 1 N/m2
1 atm = 760 mmHg = 760 torr
1 atm = 101.325 KPa
Table 1.0 Characteristic Infrared Absorption frequencies
Bond
C-H

Compound Type
Alkanes
CH3 Umbrella Deformation

C-H Alkenes
Aromatic Rings
C-H Phenyl Ring Substitution Bands
Phenyl Ring Substitution Overtones

Frequency range, cm-1


2960-2850(s) stretch
1470-1350(v) scissoring and bending
1380(m-w) - Doublet - isopropyl, t-butyl
3080-3020(m) stretch
1000-675(s) bend
3100-3000(m) stretch
870-675(s) bend
2000-1600(w) - fingerprint region
3333-3267(s) stretch

C-H Alkynes
700-610(b) bend
C=C Alkenes

1680-1640(m,w)) stretch

CC Alkynes

2260-2100(w,sh) stretch

C=C Aromatic Rings

1600, 1500(w) stretch

C-O Alcohols, Ethers, Carboxylic acids, Esters

1260-1000(s) stretch

C=O Aldehydes, Ketones, Carboxylic acids, Esters 1760-1670(s) stretch

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Monomeric -- Alcohols, Phenols


O-H Hydrogen-bonded -- Alcohols, Phenols
Carboxylic acids
N-H Amines

3640-3160(s,br) stretch
3600-3200(b) stretch
3000-2500(b) stretch
3500-3300(m) stretch
1650-1580 (m) bend

C-N Amines

1340-1020(m) stretch

CN Nitriles

2260-2220(v) stretch

NO2 Nitro Compounds

1660-1500(s) asymmetrical stretch


1390-1260(s) symmetrical stretch

v - variable, m - medium, s - strong, br - broad, w - weak

THIS IS THE END OF THE LABORATORY MANUAL ~

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